Strategic Reset Workshops for Scaleups
- Laura Derbyshire
- 2 days ago
- 5 min read
Why high-growth businesses need clarity, not another planning day
There’s a point in a scaleup’s life where everyone agrees something needs to change, but no one is quite sure what.
Growth has slowed or feels harder than you're used to, the leadership team is busy, but momentum feels diluted. It feels like there are too many initiatives, too many priorities, too many “we should probably…” conversations.
This is usually when someone suggests a strategy day, which can either be exactly what you need or a complete waste of time.
In my experience - and having run plenty of these - the difference isn’t effort or intent, it’s whether the business is actually ready for a strategic reset, not just another planning exercise or even worse, a load of decks prepared by SLT that you all go through whilst chomping on brownies and sipping nice coffee in a place it took two hours to get to.
The problem with most strategy workshops
Many scaleups lack alignment. Typical symptoms look like this:
Different leaders have different definitions of growth
Marketing is optimising activity, not direction
Sales and product are solving different problems
The strategy hasn’t been re-decided since the last funding round
Everyone agrees “something feels off”, but can’t articulate why
In this context, traditional strategy workshops often fail because they focus on outputs instead of decisions.
We've all been there; post-it notes multiply, Haribos are eaten, frameworks are filled in, energy is high, and then Monday arrives - and very little actually changes.
What a strategic reset actually is
A strategic reset isn’t about starting again, and it’s definitely not about team bonding - it’s about creating shared clarity at a moment when the business has done enough growing to need a new level of thinking.
For scaleups, a reset usually means:
Re-aligning the leadership team around what matters most now
Stress-testing assumptions that no longer hold
Clarifying what the business is really optimising for
Deciding what to stop doing, not just what to start
Reconnecting strategy, brand, and execution
It’s less “five-year plan” and more “are we still pointing in the right direction?”
Why scaleups need resets at specific moments
From experience with our clients hosting short strategic alignment sessions in their office or longer offsite strategic resets, they tend to be most valuable when:
Growth has plateaued after early success
The company has raised funding, and expectations have shifted
The leadership team has grown or changed
The market has evolved faster than the narrative
Execution is strong, but impact is inconsistent
At this stage, optimisation alone won’t unlock the next phase. The business doesn’t need to run faster - it needs to re-decide where it’s going.
From strategy to flow
This is where many leadership teams get stuck, and it is something that I am passionate about.
They know clarity matters, but they’re too close to the business to see it clearly. Conversations often start to loop, decisions get deferred, and everyone just defaults back to execution. This is why stepping out of the day-to-day matters, not necessarily for inspiration, but for perspective.
The most effective strategic reset workshops create the conditions for flow:
Space to think without interruption
Structured conversations that surface real tensions
External facilitation that challenges assumptions• Enough calm to join the dots, not just react to them
Flow isn’t some soft skill from woo-woo land. It’s productive, needs to be taken seriously, and enables leadership teams to make better decisions faster and with greater confidence.
What a good strategic reset produces
When done properly, a strategic reset doesn’t end with a long document that looks great (but no one ever reads again); it crucially needs to move through to activation plans in order to move the dial for the business:
Clear strategic priorities
Aligned leadership narratives
Sharper positioning and focus
Better briefs for marketing and agencies
Fewer initiatives, executed with intent
Most importantly, it restores momentum through clarity.
Strategy as a leadership responsibility
At the scale-up stage, strategy isn’t something you delegate to a document or a department; it’s a leadership responsibility.
That doesn’t mean founders and CEOs have to have all the answers; it means creating the space to ask better questions and being willing to hear uncomfortable ones.
A strategic reset is often the moment where a business stops reacting to growth and starts shaping it again.
Where OSER fits in
At OSER, we work with scaleup leadership teams at precisely these moments.
Our strategic reset workshops and Flow Retreats are designed for founders, CEOs and senior teams who need:
Clarity on direction
Alignment across leadership
Strategic thinking grounded in commercial reality
Space to think and the structure to decide
We provide ambitious founders and CEOs with decision-focused, outcome-led sessions built around the real challenges of scaling in an AI-shaped, high-pressure environment.
Who leads OSER’s strategic reset workshops
OSER’s strategic reset workshops and Flow Retreats are curated and led by Laura Derbyshire and Diego Chicharro, bringing together senior leadership perspectives, strategic clarity, and an effectiveness-led growth lens.
Laura is the founder of OSER and a former senior marketing leader and board advisor, with over 20 years’ experience helping scaleups and leadership teams clarify strategy, reposition brands, and unlock new growth. She has led numerous strategic workshops, including with Citywire on global brand positioning and new revenue streams, and with Bayley & Sage on aligning long-term growth plans, commercial five-year goals and the development of their online business.
Diego is an ex-Publicis Head of Effectiveness and Global Strategy Director, specialising in brand positioning, category entry points and distinctive growth strategies. His work spans major brands including Morrisons, P&O Ferries and Taco Bell, and has been recognised with multiple Effie Awards for effectiveness.
Together, Laura and Diego bring a rare combination of strategic clarity, creative thinking and commercial effectiveness, ensuring OSER’s strategic reset workshops are grounded in real-world growth challenges, not theory.
If your leadership team is at a point where clarity matters more than activity, OSER’s strategic reset workshops and Flow Retreats are designed to help you step back, realign, and move forward with confidence.
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FAQs: Strategic Reset Workshops for Scaleups
What is a strategic reset workshop?
A strategic reset workshop helps scale-up leadership teams step back from execution to realign on strategy, priorities, and direction. It focuses on clarity and decision-making rather than planning activities.
When should a scaleup consider a strategic reset?
Common triggers include slowing growth, leadership misalignment, post-funding transitions, market changes, or a sense that execution is busy but unfocused.
How is a strategic reset different from a strategy away day?
A strategic reset is decision-led and outcome-focused. Many strategy away days prioritise ideas or team bonding, whereas a reset is about alignment, focus, and strategic trade-offs.
Can strategic reset workshops be run at any time of year?
Yes. Strategic reset workshops are most effective when they respond to a real business moment, not a calendar date. Many scaleups run them mid-year, post-fundraise, during periods of rapid change, or when growth starts to feel heavier. The right time is when clarity is needed, not just in January.
Who should attend a strategic reset workshop?
Founders, CEOs, and senior leadership teams. These sessions work best when the people responsible for direction and growth are in the room.
What outcomes should a scaleup expect from a strategic reset?
Clear priorities, aligned leadership thinking, sharper positioning, and a stronger foundation for marketing, growth, and execution.
How do Flow Retreats support strategic resets?
Flow Retreats are designed to create the space and structure leaders need to think clearly, connect the dots, and make confident strategic decisions, away from daily pressures.
